title: Ready preparation of furanosyl n-pentenyl orthoesters from corresponding methyl furanosides.
abstract: The 3,5-di-O-benzoyl n-pentenyl orthoesters of the four pentofuranoses have been prepared. The first key intermediate in each case is the methyl pentofuranoside(s), and a user-friendly procedure for the preparation of each, based on the Callam-Lowary precedent, is described, whereby formation of the crucial α/β anomeric mixture is optimized. The mixture is used directly to prepare the corresponding perbenzoylated pentofuranosyl bromide(s) and then the title compounds.
authors.affiliation: Natural Products and Glycotechnology Research Institute, Inc., 595 F Weathersfield Road, Pittsboro, North Carolina 27312, USA.
authors.forename: Changalvala V S
authors.initials: CV
authors.lastname: Ramamurty
authors.forename: Parimala
authors.initials: P
authors.lastname: Ganney
authors.forename: C Srinivas
authors.initials: CS
authors.lastname: Rao
authors.forename: Bert
authors.initials: B
authors.lastname: Fraser-Reid
mesh_terms: D004952:Esters; D006017:Glycolipids / Q000737:chemistry*; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000737:chemistry
chemical_list: D004952:Esters; D006017:Glycolipids; D006842:Hydrocarbons, Brominated